Chlorotrimethylsilane → HCID 54532677, compound

HRID 2058280Notes

Reaction equation

HRID 2058280 reaction equation
C[Li].C(NC(C)C)(C)C.[C:10]1([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl[Si:23]([CH3:26])([CH3:25])[CH3:24]>C(OCC)C>[CH2:20]([O:19][C:17]([O:18][Si:23]([CH3:26])([CH3:25])[CH3:24])=[CH:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:21]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7590Ethyl phenylacetateHCID 7912DiisopropylamineHCID 178418348HCID 178418348, compound

Product 1

HCID 54532677HCID 54532677, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-78 °C

Procedure

Methyllithium in diethyl ether (0.25 mol, 140 ml of 1.8 M solution) was added dropwise to a solution of 27.6 g (0.27 mol) of diisopropylamine in 40 ml of diethyl ether. The reaction mixture was cooled to -78° C. and 26.3 g (0.16 mol) of ethyl phenylacetate were added dropwise. The reaction mixture was warmed to 0° C. and 46 ml (0.36 mol) of chlorotrimethylsilane were added rapidly. The reaction mixture was stirred overnight at 25° C., filtered to remove LiCl, and then distilled under reduced pressure to give 24.91 g (66% yield) of β-ethoxy-β-trimethylsiloxystyrene as a colorless liquid: bp 92° C. (0.7 mm); 1H NMR (CFCl3) δ 0.0 ppm (s, 9H), 0.94 ppm (t,J=7 Hz, 3H), 3.44 and 3.63 ppm (qs, J=7 Hz, 25:75, 2H), 4.17 and 4.36 ppm (ss, 25:75, 1H) and 6.57-7.20 ppm (m, 5H). Anal. Calcd. for C13H20O2Si: C, 66.05; H, 8.53; Found: C, 66.26; H, 8.88.

Workup

  1. temperatureThe reaction mixture was warmed to 0° C.
  2. filtrationfiltered
  3. customto remove LiCl
  4. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-d3afc64986fc450cbc9133ce25bf3f3f
Source dataset
uspto-grants-1980_07
Patent number
US04215044

Reaction notes

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